New vat dyestuff and process of making same



Patented Feb. 17, 1931 1 UNITED sTAras PATENT FFICE HEINZ SCHEYER, OF RIO DE JANEIRO, BRAZIL, ASSIGNOR TO GENERAL ANILINE WORKS, INC., OF NEW YORK, N. Y., A CORPORATION OF DELAWARE NEW VAT DYESTUFF AND PROCESS OF EAKING SAME No Drawing. Application filed. April 11, 1929, Serial No. 354,434, and in Germany April 5, 1928.

My present invention relates to new vat dyestuffs and to a process of making them, more particularly it relates to compoundsobtainable by treating Q-aroyl-p'yrazolanthrone, containing in the pyrazole ring the free imino-group and in the arylresidue a halogen atom in ortho-position to the ketogroup and corresponding probably to the general formula:

r of a suitable catalyst such as copper powder.

The formation of the new compounds probably takes place according to the following equation:

i. e. the hydrogen atom ofthe imino group and the halogen atom standing in ortho-po-' sition to the carbonyl group are eliminated together and form hydrogen halide, which is neutralized by the alkaline acting sub- I stance, and condensation takes place in the positions previously occupied by these-substituents. The new dyestuffs corresponding probably to the general formula:

date by acting with hydrazine on l-halogenanthraquinone-2carbonylic acids, converting the pyraZolanthrone-Q-carbonylic acid thus formed into its chloride and condensing the latter with suitable halogenated"hydrocarbons inithe presence of an acid condensing agent.

' In order to further illustrate my invention the following examples are given, the parts being by weight and all temperatures in centigrade degrees; but I wish it to be understood that my invention is not limit-ed to the examples given, nor to the exact condltions stated thereln.

E wample Ins obtained corresponds probably to the formula:

By the expression inorganic substance of a feebly alkaline reaction occurring in the appended claims, I mean an inorganic substance corresponding to an alkali metal acetate or carbonate in alkalinity. The term copper catalyst used in claim 3 is intended to include the metal itself as well as copper compounds.

I claim l. A process which comprises treating a Q-arOyl-pyrazolanthrone compound of the probable general formula:

Hal

N-NH

wherein the benzene nucleus may contain a methyl group or a further halogen atom or both these substituents, with an inorganic substance of a fee-bly alkaline reaction,

whereby the hydrogen atom of the imino group and the halogen atom standing in ortho-position to the carbonyl group are eliminated and form hydrogen halide, which is neutralized by the alkaline substance, and condensation takes place in the positions previously occupied by these substituents.

2. A process which comprises treating a 2-aroyl-pyrazolanthrone compound of the probable eneral formula:

wherein the benzene nucleus may contain a methyl group or a further halogen atom or both th substituents, with an inorganic substance of a feeb y alkaline reaction in a diluting medium while heatin whereby eondensation takes place set forth in claim 1.

3. A process which comprises treating a 2-aroyl-pyrazolanthrone compound of the probable formula wherein the benzene nucleus may contain a methyl group or a further halogen atom or both these substituents, with an inorganic substance of a feebly alkaline reaction in a diluting medium and in the presence of a copper catalyst while heating, whereby reaction takes place as set forth in claim 1.

4;. As new compounds Vat dyestuffs corresponding probably to the general formula:

wherein the benzene nucleus may contain a methyl group or a halogen atom or both these substituents.

5. As a new compound the vat dyestufi' corresponding probably to the formula crystallizing from toluene in the form of brick-colored crystals, soluble in concentrated sulfuric acid with a greenish color and dyeing cotton yellowish red shades from a violet vat.

6. Ihe process which comprises heating a mixture of about 12 parts of 2.5-diohl0robenzoyl-pyrazolanthrone of the formula:

about 120 parts of nitrobenzene, about 12 parts of dehydrated potassium acetate, about 0.6 parts of copper acetate and about 0.1 parts of copper powder at a temperature-up to the boiling point of nitrobenzene for some hours, whereby condensation takes place as set forth in claim 1.

. In testimony whereof, I afiix my si nature.

.HEINZ SOHEQYER. 

